Oak is a very strong late game Demigod.. but that's okay because a game of Demigod is often won because of good decisions made early in the game, and then capitalizing on those decisions as you level up.
In this way, Oak is beaten in the same way most others are. For instance, you were worried that he had a large force of grunts supporting him. If early on you can manage your flag control so you get warscore faster, you will ultimately deny him of these. Secondly, maintaining control of key flags, like a Deblitation flag, a +15% health flag, or similar can keep the early game in your favor, and may even result in some kills.
Lastly, knowing how to use mobility items in the game, especially Wand of Speed and Teleport scrolls can significantly up your game. These will both help you run from battle, but more importantly can let you ambush someone who is not otherwise able to fight back. Early game, oak can often fall into this category as he doesn't have many good low level abilities.